Violet mordant dyestuff and process of making same.



hurrah STATES PATENT oFiuoE.

CHARLES DE LA I-IARPE AND ERNST ."BODMER, OF BASEL, SV/ITZERLAND,ASSIGNORS TO THE FIRM 0F DYE-WOBKS, FOBMERLY L. DURAND, HUG'UENIN &(10., OF BASEL,

SWITZERLAND.

VIOLET MORDANT DYESTUFF AND PROCESS OF MAKING SAME.

No Drawing.

1'0 all whom it may concern:

Be it known that we, CHARLES DE LA TTARIPE and ERNST BoDMnn, bothchemists, citizens of the Swiss Republic, and residents of Basel,Switzerland, have invented new Violet Mordant Dyestufi's and a Processof Making Same, of which the following is a full, clear, and exactspecification.

We have found that new violet mordant dyestuffs are obtained bycondensing an amino-meta-oxybenzoylbenzoic acid substituted in the aminogroup with a pyrogallol sulfonic acid. The condensation is obtained bywarming the compounds together in a suitable medium such as sulfuricacid or bisulfate. The most suitable condensing agent is sulfuric acid,of which the concentration may vary within wide limits; an acid of percent. strength, however, is still applicable. In most cases,nevertheless, it is advantageous to use concentrated acid, becauseprolonged heating with too dilute an acid leads easily to desulfonation.Obviously, it is simplest to sulfonate the pyrogallol and to add theamino-meta-oxybenzoylbenzoic acid substituted in the amino group to themass in which the sulfonation is effected, so that the condensation mayoccur in the same operation. The operations may, however, be separate.This process is applicable to all known monoand dialkylated, benzylated,ethylbenzylated or phenylated amino meta oxy benxoyl-benzoic acids.

The same dyestuffs are obtained whether pyrogallol-monosulfo-nic acid orpyrogalloldisulfonic acid are employed, this latter reacting, in asurprising manner, with elimination of a sulfo group. Owing to this factit is possible to make without difiiculty the new dyestuffs at atemperature below 100 C. in nearly quantitative yield free fromintermixed non-sulfonated product.

The new dyestuffs thus obtained dye chrome mordanted fibers violet tobrown violet tints. They are strongly marked mordant dyestuffs. Thesenew dyestuffs are further characterized by the excellent solubility oftheir alkali salts in water.

Specification of Letters Patent.

Application filed. May 4, 1911.

Patented Sept. 12, 1911.

Serial No. 624,946.

As will be seen from the table hereinafter, the mordant character of thenew dyestuffs may be expressed by the difference of their tints on woolwith a mordant and without a mordant. ton chrome-mordanted and printedwith a discharge, the discharged places remaining quite White. They alsohave atfinity for a whole series of metallic mordants besides chromiumcompounds, for instance, iron, aluminium, tin or like compounds. Thefastness to fulling, light and sulfur of the dyeings obtained on chromemordanted wool is remarkable.

The following examples illustrate the invention.

Example I: Into a solution of 11 kilos of pyrogallolmonosulfonic acid 60kilos of sulfuric acid of 70 per cent. strength are introduced, whilestirring, 14 kilos of di methyl-amino-meta-oxybenZoylbenzoic acidcorresponding to the formula or an equivalent quantity of anotheraminometa-oxybenzoylbenzoic acid substituted in the amino group and themixture is heated to 90 C. until no further increase in the formation ofdyestutf can be observed. The cooled mass is poured into ice-water andthe dyestuff which separates in flocks is filtered and pressed. Bywarming with sodium acetate solution the sulfonated dyestuff can beseparated from a little non-sulfonated. product which is present and aquite small proportion of a basic by-product. From the filtrate fromthese substances the dyestuff is separated by adding hydrochloric acid,it is filtered, pressed and dried in the usual manner and converted intothe alkali salt.

The bodies also dye easily cot- The new dyest-uii corresponds probablylent quantity of another amino-meta-oxyto the formula benzoylbenzoicacid substituted in the 20 OH amino group, while stirrin The mixture(CH3)zN on heated to about 90 until no further 5 increase of the.formation of dyestufi? oc- I i curs. -After cooling, the mass is pouredinto ice-water and the dyestuif purified and I \O lsolated in the mannerdescribed in Example I. The same dyestuffsare obtained as 10 O areobtained by following Example I.

l i f The new dyestuffs arev brown-red to brown powders, easily solublein the form of their alkali salts to scarlet to blueish red Example II:15 kilos of pyrogalloldisulsolutions from which mineral acids precipi-15 ionic acid are suspended in 60 kilos of sultate them as red flocks oras lustrous brown furic of 66 Baum specific gravityand red crystals,appearing green by reflected mixed with 14 kilos of dimethylaminolight.The properties of a number of them meta-oxybenzoylbenzoic acid, or anequivaappear in the table hereinafter.

Colorof solution Dyeing on wool Dyeing on Dyes sitar icrflfii-sglgtifstate eats? 1 Dirnethylamino-meta-og ybenzoylbenzoio Magenta red.... RedYellowish rosc.. Red violet Violet.

ao1d+pyrogallolsulfomc acid.

2 Di-ethylamino-meta-ogcybenzoylbenzoio Magenta red.... Red Yellowishrose.. Red violet Violet. ac1d+pyrogallolsuliomc acid.

3 Mono-etl1ylamino-meta-oxyben zoylben- Scarlet Red Yellow orange..Bordeaux Brown violet.

Z010 aold +pyrogallolsnlfome acid.

4 Phenylamino-meta-0qzybenzoylbenzoic- Bluishred Red Rose Violet Brownviolet.

ac1d +pyrogallolsulfomc acid.

What we claim is: state brown-red to brown powders easily 1. Thedescribed process for the manusoluble in water in form of their alkalisalts facture of violet mordantdyestutfs, which to solutions coloredfrom scarlet to blueish 60 40 consists in condensing anamino-meta-oxyredfrom which they are precipitated by benzoylbenzoic acid substituted inthe mineral acids, soluble in concentrated sulamino group with apyrogallol sullt'onic furic acid with a red coloration turning to acid.rose yellowish or yellow orange on addition 2. The described process forthe manu of water, and dyeing chromed Wool or cot- 65 facture of Violetmordant dyestuffs, which ton violet to brown-Violet tints andunmorconsists in condensing an alkylamino-metadanted wool red-violet toviolet tints of exoxybenzoylbenzoic acid with a pyrogallol-- cellentfastness to light, fulling and sulfur. SulfOlliC acid- In witnesswhereof we have hereunto 3. Thedescribed process for the manufacsignedour names this 24th day of April 70 lure of red mordant dyestuffsconsisting in 1911, in the presence of two subscribing witcondensing adialkylaminormetaoxybenzoylnesses. benzolc acid with apyrogallolsulfonlc acid. CHARLES DE LA HARPE.

4. As new products, the described dye- ERNST BODMEI, stuffs resultingfrom the condensation of a pyrogallol sulfonic acid with anaminolVitnesses:

metaoxybenzoylbenzoic acid substituted in AMAND BITTER, i the aminogroup and constituting in dry ARNOLD ZUBER.

Copies .of this patent may be obtained for five cents each, byaddressing the Commissioner of Patents, Washington. D. C.

